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Head of Operations

OpenTrack

midpermanentoperationsproduct-management Chicago, Chicago, Illinois, United States 2 days ago via RemoteOK

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Tags

OperationsProject ManagementStrategic PlanningKPI TrackingCross-functional LeadershipProcess ImprovementStartup OperationsBusiness AnalysisStakeholder Management

About the role

Role Overview

Head of Operations at OpenTrack, acting as an extension of the CEO to drive strategic initiatives and ensure execution. The role owns cross-functional operations, project management, and communication to keep the CEO focused on the highest-leverage priorities.

Responsibilities

  • Partner directly with the CEO and leadership team to drive strategic initiatives and execute company priorities.
  • Serve as the CEO’s operational proxy: own decisions, communications, and workstreams on the CEO’s behalf.
  • Own end-to-end cross-functional project management for high-impact initiatives (planning through execution).
  • Triage and manage incoming requests and open items directed at the CEO (filter, delegate, resolve independently where possible).
  • Define, document, and operationalize company-wide processes to improve efficiency and alignment.
  • Act as a central communication hub to ensure clarity and coordination across teams.
  • Identify operational bottlenecks and proactively implement solutions.
  • Track progress against company goals, KPIs, and strategic priorities; surface risks and course-correct.
  • Conduct analysis and research to inform business strategy, partnerships, and growth opportunities; deliver clear recommendations.
  • Serve as a trusted advisor and sounding board to the CEO on strategic and operational matters.

Qualifications

  • 3–6 years of experience in a high-growth startup environment, consulting, operations, or strategy.
  • Strong written communication and organizational skills.
  • Strong analytical and problem-solving skills; ability to synthesize complex information into clear insights.
  • Exceptional project management skills; able to manage multiple priorities simultaneously.
  • Strong business judgment; comfortable operating independently in ambiguous environments.
  • Demonstrated ability to represent senior leadership and own outcomes.
  • Strong communication and interpersonal skills; ability to collaborate across teams and levels.
  • Strategic mindset with a bias toward action and execution.
  • Detail-oriented with a commitment to accuracy and operational excellence.
  • Ability to thrive in a fast-paced, dynamic startup with rapidly evolving priorities.

About OpenTrack

OpenTrack is a logistics technology company tackling fragmented logistics data and workflows. Using real-time data from hundreds of sources, it provides an AI logistics workflow builder, enterprise web application, API services, and a white-label portal for freight visibility, performance metrics, and predictive insights.

Scraped 7/26/2026